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How to Wear Ankle Boots With Skirts – Style Guide

Many of us wonder how to wear ankle boots with skirts when we add this versatile boot to our wardrobe. It can be tricky to know which type of ankle boots to pair with the various styles of skirts to create stylish outfits, as there are so many to choose from!

To help, here is an ankle boots and skirts style guide (including pictures!) to cover as many bases as possible, so you look put-together every time you style this fashion duo.

First let’s start with some basic style guidelines, before we get into the best ankle boots to wear with each style of skirt.

How to wear ankle boots with skirts

How to wear ankle boots with skirts

Wear chunky, low-heeled ankle boots with casual skirts for an easy day-time look. Pair sleek, heeled ankle boots with elegant or business wear skirts, such as midi or pencil skirts, for a more formal style.

The above is a good rule of thumb to follow when pairing your ankle boots with your skirts, to make sure your outfits are appropriately styled.

For a casual day time look, chunky ankle boots in brown or black look great with above the knee skirts, such as denim, or jersey-material skater skirts.

When you want to look a bit more dressed up, wear heeled ankle boots with a shaft that fits to your calf, with a more elegant style skirt. This style of ankle boot is a perfect option for the office, if your workplace has a smart casual dress code. Match your boots with a pencil skirt or a knee-length skirt for a presentable and seamless style. Pair with tights in the cooler months to look even more put-together.

How to wear ankle boots with denim skirts

For casual day time outfits wear ankle boots with light wash or indigo wash denim skirts and a crop top, or with a jumper and tights in the cooler months. Wear black, heeled ankle boots with a black denim skirt and a nice top for a more dressy evening look.

Ankle boots with denim skirts

In the above picture I styled three different looks with my ankle boots and denim skirts, to show how versatile this pairing can be.

For a simple day time look wear a mustard sweater with a classic denim skirt with your ankle boots. Finish off the outfit with a chunky belt and a monochrome bag.

If you want to dress up your denim skirt, pair it with ankle boots that have extra detail. For the middle and right-hand outfits I styled ankle boots with a gold heel, for a pop of metallic contrast. I chose red as the focus colour for the outfits to create dressier variations for this pairing.

How to wear ankle boots with midi skirts

When pairing ankle boots with midi skirts, opt for a sleek style of boot with a tall shaft that fits to the calf. Choose heeled ankle boots over flat, as they will elongate the legs and accentuate the silhouette of the skirt.

Ankle boots with midi skirts

Midi skirts look great with heeled shoes, and ankle boots are no exception. There are so many styles of ankle boots available, that it’s really easy to get your hands on a more elegant pair, to match with your dressier skirts.

In the above image I paired my black heeled ankle boots with three different midi skirts and tights, for a more formal twist on this boot.

How to wear ankle boots with long skirts

When wearing ankle boots with long skirts make sure the boots are heeled, and the hem of the skirt doesn’t pass the shaft of the boot. Showing off your ankle boots instead of swamping them in material creates a much more stylish look.

Ankle boots with longs skirts
Sources: Unsplash/ ©[Elias De Carvelho] via

In the above image you can see how two more formal looking shirts are paired with sleek ankle boots for a stylish twist. Ankle boots are typically considered a more casual shoe, but when styled right with a dressier long skirt they can look fantastic.

Black, heeled ankles boots with a tall shaft are the easiest style of ankle boots to pair this way. Brown heeled ankle boots would also work well in the same way for the warmer months, with white, cream and neutral toned formal shirts.

How to wear ankle boots with short skirts

When wearing ankle boots with short skirts choose a lower heeled boot for casual, day-time short skirts and heeled ankle boots for dressier short skirts in the evening. If you are wearing tights with your short skirt match the boots to the colour of the tights. If not, match the boots to the colour palette of your skirt.

Sources: Unsplash

In the above image lighter coloured ankle boots are paired with lighter toned and natural toned short skirts, to create stylish pairings within the same colour palettes that look great in summer.

In the below image black ankle boots are paired with with black, denim or neutral short skirts, for three put-together styles. The left-hand outfit is suitable for an evening out, the middle for a smart casual event and the right for transitioning between the seasons.

Sources: Unsplash

How to wear ankle boots with a pencil skirt

When pairing ankle boots with a pencil skirt avoid chunky styles and opt for a sleek, heeled boot to elongate your legs and match the seamless silhouette of the skirt.

For bonus points match the boots to the colour of the skirt to create a cohesive colour palette.

Red cropped jumper black pencil skirt

In the above image I paired a black pencil skirt with heeled black ankle boots, tights and a red cropped jumper. I finished off the look with a red bag to tie everything in together. This outfit is on the smart casual side, and would work well for the office.


How to wear ankle boots with skirts and tights

When wearing ankle boots with skirts and tights match the colour of your ankle boots to the colour of your tights, for a more put-together and seamless outfit. Pair chunky ankle boots with casual skirts, and sleek, heeled ankle booties with more elegant skirts.

Ankle boots with skirts and tights

In the above image I paired three different skirts with black tights and black ankle boots, to show how versatile ankle boots and tights can be when worn with skirts. Tie your outfits together with accessories to match the colour of your boots, such as a chunky black belt.

Ankle boots with tights and skirts is a great outfit style for the autumn and winter months, and is an easy way to transition your skirts between the seasons. Ankle boots can be worn so easily with skirts when styled this way, for both casual and more dressy outfits.

How to wear flat ankle boots with skirts

When wearing flat ankle boots with skirts choose skirts with a shorter hemline for a more casual look. Long skirts can look a little odd with flat ankle boots, as a longer hemmed skirt typically appears more formal, whereas a flat ankle boot is a more casual shoe.

If your long skirt is a more relaxed style, and isn’t intended for smart casual or business casual wear, then you can pair it with a flat ankle boot for a relaxed look.

A great example of a stylish, but relaxed flat ankle boot is the Chelsea boot, which looks great when paired with a slouchy jumper over a long casual skirt, for an off-duty celebrity style.

A note

Thank you for reading this ‘ankle boots and skirts guide‘ – I hope you now feel excited to head to your wardrobe and put together some easy outfits!

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